I see that there's some book out about Simon Cowell. It drives me mad that, despite being richer than Croesus, he appears to own only two outfits. Does this mean I'm going to have to endure even more photos of the man than usual in the press and therefore be driven even madder?

Marcus, London

By "only two outfits", you are referring, of course, to Cowell's two uniforms du choix, a black or white T-shirt with jeans or a half-unbuttoned white shirt with jeans. Cowell is by no means the only man who sticks to a rigid and decidedly boring uniform; heck, he's not even the only rich man who does it. Male fashion designers, rather bizarrely, are especially fond of, to use a particularly irritating example of fashion lingo, "working" a single look. Just off the top of my head, Giorgio Armani, Karl Lagerfeld and Roberto Cavalli have only been seen in one single look each for the past several decades: respectively, black T-shirt and jeans (v Cowell), a tight black suit, and a black blazer worn with copious amounts of crocodile skin and a burnished tan.

Taking a little sidetrack here – a fashion slip road, if you will – you might think it odd that the folks at the vanguard of an industry predicated on convincing people that they should entirely overhaul their wardrobes every six months should, themselves, be so rigid in their personal style, but that is to miss the perverse nature of fashion. You see, whatever the masses are doing is the opposite of what the Fashion Insider is doing. Thus, while the (sniff!) public is absolutely encouraged to change their outfits hither and thither, the Fashion Insider proves his difference from these … these … peasants by his unswerving fidelity to his look, no matter how ridiculous it may be.

This, though, is not the method that lies behind Cowell's monotonous wardrobe. Rather, I suspect his modus operandi lies closer to that of a friend of mine who, for purposes of maintaining his friendship beyond today, I shall refer to as "Mark". "Mark" is a very lovely chap: talented, kind, smart blah blah blah. I have known Mark for many, many a year and, oh, I muse, with a fond shake of my head, haven't we seen each other through thick and thin. One thing I have not done, though, is see him in any outfit other than a white T-shirt and a pair of blue jeans. No matter what the climate, or occasion, it's always a white T-shirt and a pair of Levi's.

For a while, I assumed that Mark's attitude to his clothes was the same as mine to my breakfast: stick with the same thing every day so you don't have to bother thinking about it. But then I realised there was more to it than that, more of a mix of fear of fashion combined with bullish defiance.

As I have written about many, many times before, men often feel they have less room to manoeuvre in fashion than women do and this makes them behave in the oddest of ways. Some dubious sorts get their kicks by siphoning off their fashion urges into ridiculous things like expensive watches, oversized belt buckles or costly trainers. Some go in the opposite direction and plump for ornate styles (Hawaiian shirts, brightly coloured trousers), really sticking it to the man – yeah! And others, like Simon and "Mark", stay exactly in one single place.

They see it as playing it safe, avoiding accusations of fussiness or questions about their sexuality, while sticking firmly with what they know. I see it as fashion constipation. Whatever, they seem comfortable with it and, frankly, I think "breaking out of one's comfort zone" is a hugely overrated concept.

The real issue with Cowell's look is whether it makes you think of all the hot, very hetero sex the man is getting all the time. For what seems like an eternity but may in fact have been only a fortnight, tales of Cowell's amazing – and very hetero – sex life have flooded the tabloids like a burst sewage pipe, each one outdoing the one from the day before. The climax, if you will, was surely reached this weekend with Alicia Douvall's claim that not only did they have sex 11 times in one night but that Cowell "would analyse my performance just like a judge on the TV and say how there could be an improvement next time". It's like they don't even care if we believe all this or not, isn't it? Or maybe this is all one giant satire by Craig Brown. That, frankly, feels like the only plausible conclusion.

Still, at least Simon's got his monochrome look, which obviously proves how macho and hetero he is, right? Well, either that or a fashion designer.